


Winchester's Rouge

by almaasi



Category: Supernatural
Genre: Angsty Schmoop, Childhood Memories, Dean in Makeup, Dean in Panties (mentioned), Gen, Past Character Death, Personal Growth, Self-Acceptance
Language: English
Status: Completed
Published: 2013-12-14
Updated: 2013-12-14
Packaged: 2018-01-04 15:14:15
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,702
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1082534
Author URL: https://archiveofourown.org/users/almaasi/pseuds/almaasi
Summary: <blockquote class="userstuff">
              <p>Someone left a bag of makeup in the motel bathroom. Sam went out, so Dean's alone - and he wants to try it on. But for him, it's not as simple as just going for it.</p>
            </blockquote>





	Winchester's Rouge

**Author's Note:**

> Set around the season 2 / season 3 era.

Dean could hear the buzzing from the dentist’s room, that tiny little toothbrush whizzing around Sam’s mouth. In the waiting room where Dean sat, a plastic clock ticked, and everything was just a little too dusty to be trustworthy.

Dean wished they had gone somewhere fancier. He couldn’t remember the name on their current credit card, but Sam had insisted that even with fake cards, it wouldn’t be a wise move to ping anyone’s radar. So, crappy back-alley dentistry offices it would be.

Dean crossed his fingers and hoped the framed credentials on the waiting room wall were real.

A few slow minutes passed, wherein Dean worried whether Sam would need fillings, whether Dean himself would need fillings, whether the dentist or their assistant would be hot. There was too much to think about. Sadly, being a hunter didn’t stop him from being human. Cavities and endless things to fret over, that was his life.

Taking a deep breath to cleanse his thoughts, Dean turned his eyes to the narrow table a few seats down from him.

There were a couple of car magazines, which Dean would have reached for without hesitation had he been anywhere else. But the copies were rag-eared and almost certainly smothered in germs. The stained brown walls and the uncovered pipes draped with towels were bad enough to look at; he didn’t have the stomach to touch anything in here with his bare hands.

Under the mucky magazines, however, there was something that looked new in comparison, its spine uncracked and its corners unbattered. Glossy, dainty whiteness in a zoo of dark and bold. It seemed like relief to Dean, seeing something safe.

He knew what it was, and it wasn’t anything to do with cars.

He thought about not picking it up, just leaving the damn thing alone - he really did - but he was well-enough acquainted with himself that he already knew that resolve wouldn’t stick. He wanted to look. Curious, that’s all he was.

He glanced around, just to check nobody was watching him; he was the only person waiting. The dentist chuckled something unintelligible to Sam in the next room, and Dean heard Sam’s mumbled reply.

Awkwardly rolling his eyes in case he somehow embarrassed himself, Dean’s fingers pinched for the single magazine. He slid it out from the others, which slopped out of their messy pile. Dean had no intention of neatening them up.

He looked at the cover of the magazine. There was a very beautiful woman on the cover, doe-eyed and puffy-lipped, with skin so completely flawless that Dean automatically assumed she was half human, half Photoshop. Her perfect hair and strange pose covered the title at the top, so Dean had no idea what the publication he was looking at was called.

With a careless sigh, he flipped open the first few pages, pretending not to look closely. Bright colours against white made up every spread, with the occasional full-page photograph of a well-dressed woman.

He was used to seeing women in magazines stark naked or in underwear, not in suits, looking pristine and... well, _smart_. While it was a refreshing change, he felt guilty and squirmy deep inside; he wasn’t meant to look at this sort of crap and he knew it. It wasn’t meant for him.

Self-conscious, his eyes darted to the side of the waiting room instead, to a corner beyond which he knew there was a middle-aged secretary reading a magazine of her own. Nobody could see what Dean was looking at, nobody would know.

Blinking, he returned his focus to the pages before him, spread open on his hands. Delving further in, he saw photos of dresses and skirts cut out with no background, italic captions at their edges with pricing and the name of the seller.

He raised his eyebrows. Surely nobody in their right mind would pay $200 for a coat that looked like it came from a thrift shop. He leaned back in his creaky chair, scoffing at the fact that every item shown in the magazine was about that price.

He flipped through pages, mildly interested. He felt like he was looking through a peculiar lens, one that analysed and scrutinised but didn’t quite get involved, not the same way he would for a magazine filled with pictures of classic cars. Perhaps that was what demographic aims were for, after all. Dean wasn’t some high-maintenance pencil-skirted lady on the up-and-up, so this wasn’t his regular reading material.

...But that didn’t mean nothing in here captured his attention.

He chanced upon the section about makeup, which initially seemed intent on bullying celebrities, nit-picking the kinds of flaws all humans had. God, even _Dean_ had wobbly bits, and he was an active man in his mid-twenties.

It was nearly repulsive to him to realise that people actually sat behind desks and tore apart the people they supposedly idolised. He couldn’t complain about some good ol’ rage against the machine (or criticising your leaders, for that matter), but this wasn’t it. He sneered and turned the page, putting it out of his mind.

The next heading read _Choosing the Best Makeup Style for Your Eye Color_.

Hmm, Dean thought. He skim-read the introduction, folding the page back so his palms wouldn’t stick to the outside gloss any more. He hooked his ankle up over his knee, getting comfortable.

He decided that seeing eyes referred to as “peepers” was the most ridiculous thing he’d ever seen in supposedly _serious_ print. He was almost grinning, but the disdainful frown wasn’t leaving his face.

The guilty feeling slowly alleviated. He wasn’t reading for personal interest any more, but just so he could laugh at what he read. He might even tell Sammy about it later, it might make him laugh too.

On the second half of the page there was a section divided into rows, showing pictures of eye colours, and thoroughly dismantled pots of eyeshadow. What was the point of expensive makeup if the photographers just smashed it up and tipped it out of its tray?

Still, he didn’t stop his gaze from drawing down the list, then to the following page, landing on “green eyes”.

_We all know that green is gorgeous. Green eyes have all the beauty of nature’s best behind them, so it’s no surprise that when we want to accentuate that color, all-natural shades are the way to go. Whether you’re looking to dazzle in daylight or sway in the smoky shades of night, there’s a great color out there to suit your sparklers._

Dean harrumphed, pursing his lips. He kept reading, somehow finding himself legitimately curious, despite the weirdness that came with that.

He finally landed on something that translated clearly, rather than in annoyingly seductive prose.

_For summer greens:_  
 _Make your eyes stand out with **warm hues** to complement and flatter your colour. For bold and beautiful, try **aubergine** or **purple**. For smoky and sultry, go with a **neutral taupe** paired with **brown** or **black** eyeliner. For riveting and wild, try out some different shades of **green** to discover which makes your eyes pop!_

There was more detail, but that was the gist of it.

Purple, brown, black, green.

✩✩✩

Years passed.

It was trivial information, but it stuck with Dean. He picked clothes that played into those colours; neutral browns, greys; warmer shades of red. His green utility jacket was his favourite - he never mentioned to anyone why he favoured it on so many hunts, but it was because when they finally got back to their motel room, he could look in the mirror and still see a spark of something that looked decent.

Green eyes.

Purple, brown, black, green.

✩✩✩

“Dibs on the first shower,” Sam said, the moment they got into their motel room. “Ugh, something is crusting on my ankles, I can feel it.”

Dean tossed his duffel bag on the bed furthest from the door. “Not fair, you cheated.”

“You can’t cheat at calling dibs,” Sam said, removing his monster-gunk-mottled jacket and putting it safely into a plastic bag for washing later. “Just let me take the first shower, I’ll be quick, promise.”

Dean was usually happy to let Sam take the first anything, get the best bed, the biggest slice of pie. But today Dean really, really needed to get the ooziness off his skin. He hated it, it was almost gross enough to make him panic.

Sam must have seen the flash of emotion that crossed Dean’s face, and his expression turned soft. He raised a fist with his other hand plateaued under it. “Paper scissors rock.”

Dean sighed; Sam was still going to get the hot water. Paper scissors rock was just an excuse for Dean to lose on purpose and give Sam the nice things. Pointless, maybe. But if Sam wanted the first shower, Dean would let him have it, even if Dean ended up sleeping with something oily trickling into his jeans.

They tapped their fists on their hands, one, two, three―

Dean gaped. “What?”

Sam was smirking. “You win. Scissors beats paper, man.”

Dean shut his mouth. Sam always played rock, that was how Dean always lost. And now Sam had just... _handed_ this to him?

Dean jittered slightly. “Uh. Thanks, man,” he said, bewildered. Turning away, he grabbed some clean clothes out of his duffel.

He grinned at his bed, seeing the little machine by its side. He thumbed towards it, and chuckled to Sam, “Awesome. They’ve got Magic Fingers.” Sam forced a smile, but Dean only grinned harder, knowing that just the mention of a vibrating bed reminded his little brother of things he ought never have seen, yet had seen one too many times.

Still feeling smug, Dean went into the bathroom. Two white towels were folded on the wide ridge behind the sink. Dean dumped his clean clothes on the floor, since there was nowhere to hang them.

Relief flooded through him as he stripped, removing the sticky, gooey grossness his clothes had accumulated over the day’s hunt. _This_ was why Dean preferred to book a room _before_ they went out killing monsters. Thank god the people at the front desk didn’t ask questions when Sam went in a few minutes ago.

Down to his boxers now, Dean raised his eyes and stood up straight, checking his face for injuries in the mirror. Hm, no more than a bruised cheek, nothing that wouldn’t stop smarting in a day or two. Mucky splatters covered his stubble, though, and he wasn’t keen to let that linger in case it was poisonous or hallucinogenic.

He noticed a black pouch tucked between the towels and the side wall, and he assumed there was free shampoo in there. He loved that stuff, especially the kind that smelled like honey. He grabbed the pouch with a swipe, unzipping it to pull everything out at once.

He stopped when he realised there was absolutely no shampoo in there at all. Instead, the pouch was filled with several small black plastic trays with clear lids, a few round pots, an oddly-shaped packet or two, and a set of slim pens.

He’d grabbed someone’s makeup kit.

Maybe the previous guest left it behind, maybe it belonged to the maid, maybe they were in the wrong room, maybe he should just put this down and walk away, get in the shower and wash this crap off him, maybe he shouldn’t still be _holding_ this―

His breath shook out of his throat and he put the pouch back where he’d found it.

Oh god, no - not there. No, Sam might find it there. Picking it up again, Dean zipped it up carefully, fingering its lace sides. It was a nice pouch, decorative. Soft under his hands, too.

He looked around himself, seeing grubby tiles under his feet, the toilet with the lid down, the door behind him without so much as a hook.

His searching eyes chanced upon the basin in front of him, which had a sleek tree-trunk of porcelain keeping it off the ground. There was a little space behind that, he could hide it there.

He crouched and nudged the pouch until it couldn’t be seen.

Standing up, he set a hand over his mouth and wondered why he’d done that. He didn’t know. He didn’t know why he was all flustered and burning at the ears, toes curled and nervous. He caught sight of his reflection, startled by the childishly guilty expression.

Hand in the cookie jar, pants down. What the hell.

Swallowing hard, he looked away, turning towards the shower. He was going to wash himself and he was going to forget about it. That pouch would stay there forever and nobody would know. Maybe one day the maid would find it and claim it, and that would be that.

It was nothing to do with him.

He did as he intended; he washed up with the _actual_ complimentary soap, scrubbing until his skin stung with a glowing cleanliness. Then he wrapped himself in his towel and he went back into the main room, and he let Sam have the rest of the hot water.

And he tried not to think about it. Oh, he tried.

He drove out and got dinner for himself and Sam, and returned to their room just after the sun went down.

He handed Sam his salad wrap and he ate his own beef kebab in near-silence, broken only by a sudden realisation that he groaned aloud: “Aw, crap, I forgot to get gas.”

“We can get some tomorrow. We’re heading out to Bobby’s, right?”

Dean nodded, scuffing his mouth with a napkin. “Yeah. But I hate getting gas in the morning, everything’s pinchy and cold. Those machines bite my hands.”

Sam rolled his eyes. “You can stay in the car, then. I’ll fill her up,” he offered.

Dean smiled. He loved when Sam just accepted that Dean complained about weird things. And yet, he shook his head. “I’d rather get it now. If we gotta make a quick getaway, I’d hate to run out of gas halfway down the highway.”

Sam patted his stomach, tossing his empty wrapper onto the table. “I might as well get it, I need to run everything through the laundry anyway. You clear up, plan tomorrow’s route. We should avoid traffic.”

Dean beamed as Sam stood up, going to get his clean jacket to wear. “Hey, Sammy?”

“Mm?” Sam turned around, picking up the bag of goo-soaked clothes.

Dean stood up, licking his lips. “How long are you gonna be?”

Sam eyed Dean carefully. “Um, about an hour, less than two. Why?”

Dean’s eyes darted to the bathroom, then to his bed, then to Sammy, mouth open. Ah, crap, he’d already given away too much - Sam grimaced, but a smile pushed through.

“Enjoy yourself,” Sam said, half rolling his eyes as he made for the door. “And do _not_ use my laptop.”

“Spoilsport,” Dean snarked, so very glad that Sam had just assumed he wanted to play with the Magic Fingers. Well, he did, but that wasn’t all. “See ya, Sammy.”

Sam gave a wave, catching the keys Dean threw him, then shut the door behind him as he left.

Dean leaned back in his chair with a long sigh. He watched the door, waiting until he heard the sound of his baby’s engine juddering to life and then purring away. It never felt right to have someone else behind her wheel, but Dean did need the time alone.

His eyes wandered to the bed, where the Magic Fingers machine lay in wait.

Then his attention drifted to the bathroom door, beyond which he’d hidden a secret.

He stared.

It wasn’t his fault he thought about it sometimes. He couldn’t imagine an existence where he _didn’t_ think about dressing himself up. He’d never put names or descriptors to thoughts like that, but it was second nature for him to pick the things that looked good: clean car; well-fitted shirt.

Sometimes it went beyond that, though. He and Sam were no strangers to putting on a little makeup - to hide injuries, and to fake them. It was like art class sometimes, and like surgery other times. They didn’t think about it, it was part of their job. They were professional liars.

But sometimes, Dean would look in the mirror and wonder what kind of difference mascara would make.

Those thoughts were not common in his mind. They were fleeting, and always touched on lightly, only a vague consideration. It wasn’t that he couldn’t be bothered exploring those thoughts, but that he refused to.

He was afraid of where those thoughts might lead.

There were so many things to be afraid of in the world. He could face them all, every demon and vampire, every ghoul and clawed wraith. But there were smaller, more irrational things; heights, flying, dirt. And the more rational: losing Sammy.

Some fears he couldn’t place. They were too deep down, too thoroughly ingrained in his personality. There were parts of him - the curious part, the brave part - that wanted to force those fears away and give in. But even when he’d worked out what those fears were, he couldn’t bring himself to face them.

And so, he stood in the middle of the motel room, taking one step towards the bathroom, then two steps away, back turned. He breathed shakily, his eyes magnetised to the tiles beyond the half-open door. There was discovery to be had in there, things he wanted to try. Things he supposed he’d _always_ wanted to try, but never had the chance, nor the courage.

Nobody would see him. Nobody could laugh, or tell him he shouldn’t.

The only thing stopping him from going in there was a weak and pathetic notion in the base of his stomach, a small downward tug that said _no, you shouldn’t._

Why should he not?

He turned away, hand sliding over his forehead. He kicked his boots off, socks on the grainy carpet.

He stared at the Magic Fingers, aware there was a set of quarters in his duffel bag he’d saved for the next machine he saw. He ought to just lie back and let the vibrating bed and his own hand work him to bliss, backed by a Led Zeppelin soundtrack. That would be easy. That wouldn’t be wrong. Even Sam left him alone so he could do that.

But that wasn’t what he wanted right now. He didn’t want to miss this opportunity. He didn’t want to get a hundred miles closer to Bobby’s house and start wondering _what if_.

If he didn’t do it now, it could be years until he did.

All he wanted was to put a little on. Just see how it looked. Maybe he might see a different person in the mirror, and he was mindful as to how much he craved that.

It might even be fun.

Cupping his face in his hands, Dean let out a long breath. “You’re not a freak,” he said aloud to himself, which made him feel worse. He frowned, feeling a burst of panic. He drew in a deep, deep breath. He wasn’t a freak. He wasn’t crazy, or disgusting. He just wanted to see.

He just wanted to _try_ it.

In the end, he didn’t think about what he was doing. He consciously flipped off all inner barriers, and allowed himself to move without worry. He went to his bag, pulling out his own concealer; he needed to hide the bruise on his face.

With his towel in hand, he went into the bathroom and turned the light on, shut the door, put his towel and the little bottle down on the space behind the sink, then took the pouch from where it was hidden behind the sink. It had dust on it now, grit under the black lace, but Dean patted it off and set the bag down.

He swallowed, eyes meeting his own gaze in the mirror. He looked scared; eyebrows outward, lips apart.

What was he scared of? Self-discovery? Learning that he actually enjoyed putting on things that were meant for girls?

He already knew that, though. He liked soft things, pink things, things that were intentionally feminine. Dean was at peace with knowing that he liked those kinds of items. He liked to wear them, and he loved touching them. It turned him on, but not always; it was nice to find time to acknowledge his likes and dislikes, so on occasion he would slip into a pair of panties and just enjoy the fact he was alone and he _could_. These were his secrets, the things he would take to the grave. He was at peace with it, yes, but it was still private. Sam would never find out about the small pocket on the inside of Dean’s duffel where he kept his special clothes.

This shouldn’t be all that different. He was alone and he could. He was brave.

Taking a breath then letting it free, Dean reached for the pouch and unzipped it. Even the sound of its zipper drawing across its cloth lip made his heart leap into his throat.

He was going to experiment with this. It was going to be something he could wake up tomorrow having done yesterday. A part of his life; an event.

It felt like a turning point.

Swallowing hard, Dean tipped the bag out across the wide tiles. The pens rolled furthest, a pot toppled with a clatter then spun to a stop, a tube of lipstick clunked down without movement. One tray of eyeshadow burst open, and an applicator jumped away.

When nothing else fell out, Dean looked inside the pouch. There was a packet of makeup removal pads in there, and he unclenched his jaw in satisfaction. He put the pouch on top of his damp, crumpled towel.

Dean’s hands then spread through the contents, pushing everything apart so he could look at it. He didn’t know what all the items were, so he checked the print on the sides; the pens were eyeliner, one of which was liquid. He wasn’t sure if he’d be able to use those, fearing eye infections, as well as unsteady hands.

He stacked the pens further along the workspace, then turned his attention to the eyeshadows. With the applicator back in its place, he closed the lid of the blue powders. He had no use for blue, going by the things he remembered from years back. He wanted purple, brown, black, green.

There was a tray with a set of different colours inside: one purple, one mauve, one gold. He felt something longing turn warm in his chest; he wanted to put that on. He wanted to _wear_ it.

He gave a shaky smile, nervous, but enjoying that feeling, the desire. He’d missed that feeling in recent times.

He put that set of eyeshadows aside for later. He catalogued a set of neutral powders, of black and sparkling grey and white, then a final set, which had a larger array of colours but in far smaller allotments. There was leaf green, and peacock green, and different shades of blue and silver.

He kind of liked how it smelled, too. It was dull and fancy at once, and he could almost taste the colour. It was an exciting smell for him, and Dean realised he felt the beginnings of happiness coiled in his stomach.

He still remembered what it felt like to put on his mother’s makeup, sitting at her dresser while she picked items out for him, handing him new things to try. He grinned at his reflection, aware of how terribly he must have applied it, but still Mary told him it looked pretty.

That made it okay, Dean thought. Mary wouldn’t have minded that he liked to play with the wrong kind of toys. It made Dean happy when he was four, so Mary let him get on with it. It still made him happy at age twenty-nine, so it was fine.

Made him happy.

God, it was such a weird concept. He could call it ‘happy’, but all it really was was a fluttery, light feeling in him, the good ache that made him want to set aside the world’s problems so he could pay attention to himself. If there was a specific emotion he felt, it was more like anticipation. But he wanted to call it ‘happy’.

He smiled at himself, one side of his lips rising higher than the other. He liked to see himself smile. He liked that he wasn’t controlling it, or forcing himself to. It was just happening. He tried to stop smiling just to see if he could, but he couldn’t.

For once, it was good to fail.

Shaking his head with his lower lip under his teeth, he looked down and picked up the next thing. Mascara. A glittering thread twirled down his spine and he shivered with gladness; he definitely wanted to try that, conjunctivitis be damned. He craved longer, fuller lashes, just like all those tacky TV ads crooned about. Even if he wore them thick for only five minutes, it would be worth it.

The foundation he found was too dark for his skin, but no matter; he wanted to be able to see his freckles when he was done. There was lip gloss too, translucent and tinted pink. He lined that up beside the mascara and the eyeshadows, running his fingertips over the arranged row of containers.

He had command of a troupe here, he was captain. He was going to bring the world to its knees, today.

Empowerment coursed through him, and he let out a breath. That was all, that was everything he needed.

He spent a few minutes prepping himself - he shaved, then he went and got his toothbrush, brushed his teeth, washed his face, dried off. He watched the mirror as he dabbed concealer over the discolouration on his cheek, ignoring the twinge of pain when he blended it in with his fingers.

His freckles were covered up a bit now, but that was easier to deal with than seeing a blot in a place he didn’t want a blot. He wanted this to be perfect. This might be his only chance to feel perfect, ever.

He pushed out a long, calming breath through his narrowed lips. He was getting fidgety with excitement, his fingers wanted to grab and pull everything towards him at once, but he was going to be patient. He’d use everything one by one.

Dean started by reaching for his favourite set of eyeshadow, the purple, mauve and gold. His fingers shook as he picked up the tiny applicator, but he took a moment to control himself. With a steady hand, he ran the round-headed applicator’s clean side through the purple. He wanted to be bold, maybe the brightness of the colour would help him. He could look back on this in times of self-hatred and misery, and remember that his eyes were beautiful; the windows to his soul.

Blinking a few times, Dean leaned closer to the mirror to see as he dragged the applicator over his right eyelid. He took a second to realise he was clenching his eye too tight, and made a conscious effort to keep it relaxed, closed, his other eye open as he watched the purple spread in wrinkles over his eyelid.

It felt tickly. And nice.

Very nice.

He wasn’t very good at it, but he tried. He filled in the whole space of his eyelid, getting some purple on his lashes, but he smudged that away with a finger. He lowered the applicator so he could see how he’d done.

Oh, it was so strange. He’d never seen his eye like that. The powder was all messy around the edges, but the colour was striking. Dean blinked and turned his head from side to side, checking how it looked. His mouth remained agape, his breathing shallow.

He wasn’t sure about how it looked, wasn’t sure if it really looked okay. It was too goddamn weird.

But he closed his left eye and coloured that one in too, then checked again.

His eyes looked admittedly more girlish now, but they seemed top-heavy, as the lower half of his eyes went uncoloured. He’d seen pictures of women wearing their makeup with only their upper lid done up, but it wasn’t right for him.

He went back with the applicator and dusted a careful line under each eye, trying not to make it smudge.

He looked at it again. Yes, that was better.

His appearance was very different with that small amount of makeup on, but he was still obviously himself. He still saw his own face underneath, the same way it always looked; the purple might not have been there at all. He considered it for a while, turning his face this way and that. Eventually he decided it was time for mascara, perhaps that would add something more realistic to the oddness.

The tube of mascara squelched as he pulled the wand out. Its bristles were all in a spiral, like a miniature elongated chimney sweep’s brush. It was shiny and wet with black liquid, thick. Dean pumped the brush in and out of the bottle a few times, testing the weight of the liquid.

He wiped the bristles on the rim of the bottle, then lifted it to his eye. He paused before he touched them to his eyelashes, however, and looked at his reflection.

He still couldn’t tell if the purple really made his eyes stand out any more than usual. He had enjoyed how it felt to put it on, though. Maybe the mascara would feel the same...

He closed his right eye and swiped the wand upward past his eyelashes, feeling them gather on the brush and tug as the thick liquid transferred to them. He repeated the movement three, four times, then pulled his face away from the mirror and opened his eye to see.

His lashes felt sticky, the top ones clinging the the bottom ones. He frowned, blinking rapidly until they separated. He leaned forward again, scrutinising the new addition. There was a wet line of mascara on the skin above his eye, where he’d blinked it up. Maybe he was meant to let it dry before blinking.

He got some toilet paper from the side of the bathroom, dampening the paper under the faucet and then using it to wipe away the part he’d messed up. It came away as black dots on the paper. He looked in the mirror, glad the purple was still intact.

Dean really liked that mistake. Learning how to do this was part of the process - and it was fun, it was thrilling. Perhaps he even enjoyed the fact that this wasn’t a normal thing for a man to do. When was his life ever normal, after all?

He bit his lip as he tried again, applying the mascara with his eye open this time. It was a bit scary, seeing the brush hovering so close to him, but he had total control over it. He flicked the wand against the tips of his lashes once he was done, realising he liked how that felt, too. Tugging, almost. It was such a miniscule sensation, but a wide pleasure filled him up, just from that.

With a sigh, he smiled. His right eye was now far darker and more dramatic than his left. He blinked cautiously, satisfied when none of his lashes stuck.

He dipped the brush again, then flipped his wrist across his face and applied mascara to the top lashes of his left eye, far more slowly than the right. He wanted his eyes to match, and this angle wasn’t the easiest. He wasn’t confident enough to use his left hand, so he made do.

He shut his mouth when he realised he was gaping. Holy crap, what a ridiculous expression that was...

Finally, he put mascara on his lower lashes, but not too much, only enough that they turned blacker.

When he was done, he hummed a pleased note. He twisted the mascara tube closed, put it down, then leaned on his hands and peered at his reflection.

A part of Dean was delighted with how his makeup looked. It was subtle and loud at once. But another part of him was still unsatisfied. What was he supposed to do now? He couldn’t show Sam, no way. This activity wasn’t strictly sexual for Dean, but there was a thought in the back of his mind: he might one day like to see it that way. Like his panties. He would put them on for comfort, but sometimes... yeah, it was fun to get off while wearing them. Makeup fell into the same category.

And like panties, from a distance, Sam wouldn’t be able to tell what Dean was wearing. But that didn’t mean Dean would ever share this part of himself with his brother. This was personal on so many levels.

He wondered if one day, he might share this with someone. Someone he trusted, someone he loved. Someone special.

He looked away from himself, letting out a short, aborted breath. He didn’t let himself feel lonely, forcing the tightness in his chest away.

His eyes lingered on all the colours he hadn’t used yet. Could he try them all? Did he want to try them all?

His eyes looked so pretty like this. He felt good.

But his eyes weren’t the only part of his face he could decorate.

He reached for the lipgloss - but at the last moment, detoured to grab the lipstick. Its golden rectangular casing caught the light, shimmering long as he turned it. It fascinated him the same way it always had, the same way he remembered...

He uncapped it, swirling the base so the pointed curve of rouge poked out of the end. He inhaled, tasting the smell.

Tears sprang to his eyes immediately, his mind filled with the undisturbed memory of Mary draping pearls around his neck as he dabbed lipstick on his pouty little mouth. The smell of it was the same; dusky red, rose-warm. The smell of softness and care, of Mary’s big smile and helpful hands as they plucked the lipstick out of his hands before he dropped it.

Dean found his lip was wobbling, his mouth open, breath uneven. He blinked away the tears, hating how unexpected that had been. He missed her so much. It had been more than twenty-five years, but he still felt her touch and her arms around him as she told him she loved him.

Dean didn’t hesitate before leaning forward and touching the lipstick to his lower lip, dragging it to the side, then back again. The scent clouded his entire mind, and all he felt, all he knew, was Mary.

Mary, Mary, Mary.

Tears were sliding from his eyes and making the mascara run, but he didn’t pay that any attention. He coloured his lower lip, then pressed it to his upper one, balancing the colour. Red, as Mary’s lips were that evening she sang by the neighbour’s poolside, holding Dean’s tiny hand and swaying to the live band. A wedding, they’d been to a wedding together. Dean laughed, turning his face down, tears running without pause from his eyes, dripping onto the tiles from his chin.

She would have been glad to see him wearing her colour.

Dean capped the lipstick, then turned around and sank down the wall until he was sitting on the floor. He was grinning, and he was crying, and he couldn’t see the light through his drowning eyes. He covered his face, embarrassed by himself, but he was still happy. He didn’t _know_ what this emotion was. He’d never felt this.

He sobbed into his hands, face hurting from his smile. His fingertips were wet, his eyes were stinging from the run mascara. He curled up over his knees and took trembling, humid breaths.

He pretended his mother was beside him, chuckling at his hopelessness, draping her arm across his shoulders. She’d pet his hair and kiss his temple, then nudge his side with her shoulder. Then she would say something reassuring, but Dean couldn’t remember what her voice sounded like. He couldn’t remember what words she used, but he remembered _her_. He remembered her smile.

Dean lingered in tears for a long time. Mary was with him, and she didn’t mind if he cried. He embraced what it was like to cry for himself, missing something he hadn’t lost completely. And even more plainly, it was good to let it out.

He laughed softly and brokenly as the last of the ache drained away, and he tipped his head back against the tiles, grinning at the ceiling. His eyes felt puffy, his throat was sore, and he could taste tears. And he could taste lipstick, but that was a strengthening comfort.

He looked to his side where he’d imagined Mary, but there was nobody there. He had hoped. Yet, he was convinced she was at rest, wherever she was, and he wouldn’t bring her back from that, not even if it meant the world to him.

He ran his hand through his hair a few times, self-soothing. He sniffed, a wobbly satisfaction making its way through him, all the way to his toes. There, he thought. _That_ was why he did this. Closure wasn’t always found in the easiest or most obvious of ways. But it was found.

Mary was proud of him.

He curled up over himself and cried again, this time for reasons he didn’t bother naming. It was just... relieving. He was sticky and gross, and his eyes stung like hell, but he fought through it, letting it end when the emotion abated of its own accord.

He must have sat there for another fifteen minutes afterwards, staring at the wall. He was tired now, drained, but every moment of this had been worth it. He’d ticked off an item on the private flipside of his bucket list, as well as come to terms with Mary’s death, which he told people he’d gotten over years ago but never had.

He figured he could live his life being okay, now. Not steeped in old pains.

That would probably be bullshit come next week, but for today, right at this moment, he felt good.

He stood up, saw the muck smeared over his face, and he laughed at himself. He washed his face clean with water, then removed the leftover smears with a cleansing wipe.

There was still purple stuck under his lashes, which probably wouldn’t come off until he slept that night, and it would end up on his pillowcase. Sam wouldn’t notice, but Dean would still know it was there. He had his secrets to keep, but they were _his_ secrets. He was his own person.

He had likes and dislikes, passions and fears. He was proud of himself, yet he would condemn himself to the grave in a heartbeat out of regret, but sometimes none of that mattered. Sometimes all that mattered was that he wanted to try things for himself, and he enjoyed what he learned. That was precious to him; discovery, desire.

He couldn’t wipe the smile from his face as he packed up all the makeup. He was done for today, and he would hide the pouch again. He wondered if its owner would ever come looking for it, and whether they would ever find it.

If they ever did, they wouldn’t find their lipstick, or one tray of eyeshadow, because Dean wanted to keep those. One day he would try the other colours too, the mauve and the gold. One day he might even buy his own sets, or his own lipstick. One day he might tell somebody his funny secrets.

Right now, he knew what he liked, and he was okay with it. His mother knew, and she was proud that he’d been brave enough to try. _That_ was all that mattered.

**Author's Note:**

> Sometimes I find myself doing everyday things like flicking through a magazine at the dentist's office, seeing through Dean's eyes. What would Dean do? How would he look at this? It makes everything more interesting, for sure. And then I extrapolate. Somehow, I ended up here, writing this.  
> I wanted something where Dean puts on makeup because he wants to see what it's like, _not_ because it's sexy or he gets off on it. Honestly, I'll take character exploration over porn any day. I think that's why I find Dean's character so fascinating - there are more layers to his personality than they are over his skin.  
>  (And I cried while writing this story. Nobody ask me to explain that, I don't even understand.)
> 
> Tumblr post with a picture of Dean in his makeup [~here~](http://almaasi.tumblr.com/post/69987895989/someone-left-a-bag-of-makeup-in-the-motel).
> 
> Please leave kudos if you liked this story! It's nice to know I'm not alone in wanting this type of fic.


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